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Journal articles on the topic 'Rocaglamide synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Cai, Xiao-hua, Bing Xie, and Hui Guo. "Progress in the Total Synthesis of Rocaglamide." ISRN Organic Chemistry 2011 (April 4, 2011): 1–7. http://dx.doi.org/10.5402/2011/239817.

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The first cyclopenta[b]benzofuran derivative, rocaglamide, from Aglaia elliptifolia, was found to exhibit considerable insecticidal activities and excellent potential as a therapeutic agent candidate in cancer chemotherapy; the genus Aglaia has been subjected to further investigation. Both the structural complexity of rocaglamide and its significant activity make it an attractive synthetic target. Stereoselective synthesis of the dense substitution pattern of these targets is a formidable synthetic challenge: the molecules bear five contiguous stereocenters and cis aryl groups on adjacent carbons. In past years of effort, only a handful of completed total syntheses have been reported, evidence of the difficulties associated with the synthesis of rocaglate natural products. The advance on total synthesis of rocaglamide was mainly reviewed from intramolecular cyclization and biomimetic cycloaddition approach.

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2

Callahan, Kevin P., Cheryl Corbett, Steven Jacob, Mohammad Minhajuddin, Eleni D. Lagadinou, Randall M. Rossi, Valerie Gross, et al. "Rocaglamide Selectively Eradicates Human Leukemia Stem Cells and Synergizes with Multiple Agents to Target AML Cells." Blood 120, no. 21 (November 16, 2012): 1338. http://dx.doi.org/10.1182/blood.v120.21.1338.1338.

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Abstract Abstract 1338 Recent evidence suggests that myeloid leukemia is initiated and maintained by Leukemia Stem Cells (LSCs). Standard chemotherapy however, does not efficiently ablate LSCs. Consequently, even for leukemia patients who attain a clinical remission, LSCs are generally not destroyed and are thought to be responsible for subsequent relapse of the disease. Therefore, new treatment regimens are necessary to improve therapeutic outcomes. Nearly half of the agents used in cancer therapy today are either natural products or derivatives of natural products. The present studies demonstrate that rocaglamide, a compound derived from the traditional Chinese medicinal plants Aglaia induces robust apoptosis in primary human AML cells while sparing normal hematopoietic cells. Further analysis of progenitor cells using in vitro colony assays, as well as stem cells using the NOD Scid Gamma (NSG) xenograft model, show that rocaglamide also preferentially targets AML progenitor and stem cell populations. Methionine metabolic labeling experiments show that rocaglamide inhibits the translation of nascent protein synthesis within twenty-four hours and this inhibition results in the rapid loss of short-lived survival proteins such as c-myc, Mcl-1, and Bcl-xl. These results are consistent with previous work showing rocaglamide, and members of the rocaglamide family of compounds, inhibit translation. To investigate further the molecular mechanism of LSC-specific cell death induced by rocaglamide we performed next generation sequencing on 5 AML specimens treated with rocaglamide. Bioinformatic analysis and subsequent experiments showed that rocagalmide leads to P53 activation, NFkB inhibition, cell cycle inhibition as well as defects in mitochondrial integrity and energy metabolism. In addition to efficacy as a single agent, pre-treatment of leukemia cells with rocaglamide significantly sensitizes the cells to several anti-cancer compounds, including cytarabine and daunorubicin two of the front-line chemotherapuetic drugs for AML patients. Importantly, we show that many of the mechanistic features of rocaglamide as a single agent play a role in its ability to synergize. In comparison with translational inhibitors that are used clinically to treat AML patients, temsirolimus and ribovarin, rocaglamide is significantly more toxic to leukemia cells. Interestingly, this increased cytotoxicity does not directly correlate with ability of the compounds to inhibit translational inhibition. Temsirolimus, inhibits translation at levels equal to or greater than rocaglamide however it has a cytostatic effect on leukemia cells in contrast to the cytotoxic effects of rocaglamide. Temsirolimus also does not synergize with anti-cancer compounds to the same degree as rocaglamide. These results suggest that rocaglamide's ability to modulate several key pathways in addition to inhibiting translation are critical to the activity of rocagalmaide and may suggest ways to improve the efficacy of translational inhibitors currently used in the clinic. These studies along with preliminary in vivo pharmacodynamic and pharmacokinetic experiments indicate that rocaglamide may be a promising candidate for the development of a new class of compounds for the treatment of leukemia and for increasing the efficacy of treatments designed to specifically target AML cells. Disclosures: No relevant conflicts of interest to declare.

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3

Arai, Midori A., Yuuki Kofuji, Yuuki Tanaka, Natsuki Yanase, Kazuki Yamaku, Rolly G. Fuentes, Utpal Kumar Karmakar, and Masami Ishibashi. "Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities." Organic & Biomolecular Chemistry 14, no. 11 (2016): 3061–68. http://dx.doi.org/10.1039/c5ob02537k.

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4

Bruce, Ian, Nigel G. Cooke, Louis J. Diorazio, Roger G. Hall, and Ed Irving. "Synthesis of the carbocyclic analogue of (±)-Rocaglamide." Tetrahedron Letters 40, no. 22 (May 1999): 4279–82. http://dx.doi.org/10.1016/s0040-4039(99)00706-6.

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5

Dobler, Markus R., Ian Bruce, Fredrik Cederbaum, Nigel G. Cooke, Louis J. Diorazio, Roger G. Hall, and Ed Irving. "Total synthesis of (±)-rocaglamide and some aryl analogues." Tetrahedron Letters 42, no. 47 (November 2001): 8281–84. http://dx.doi.org/10.1016/s0040-4039(01)01807-x.

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6

Zhou, Zhe, Darryl D. Dixon, Anais Jolit, and Marcus A. Tius. "The Evolution of the Total Synthesis of Rocaglamide." Chemistry - A European Journal 22, no. 44 (September 15, 2016): 15929–36. http://dx.doi.org/10.1002/chem.201603312.

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7

Malona, John A., Kevin Cariou, William T. Spencer, and Alison J. Frontier. "Total Synthesis of (±)-Rocaglamide via Oxidation-Initiated Nazarov Cyclization." Journal of Organic Chemistry 77, no. 4 (January 26, 2012): 1891–908. http://dx.doi.org/10.1021/jo202366c.

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8

Schoop, Andreas, Helmut Greiving, and Axel Göhrt. "A new analogue of rocaglamide by an oxidative dihydrofuran synthesis." Tetrahedron Letters 41, no. 12 (March 2000): 1913–16. http://dx.doi.org/10.1016/s0040-4039(00)00021-6.

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9

Davey, Andrew E., Marcel J. Schaeffer, and Richard J. K. Taylor. "Synthesis of the novel anti-leukaemic tetrahydrocyclopenta[b]benzofuran, rocaglamide." Journal of the Chemical Society, Chemical Communications, no. 16 (1991): 1137. http://dx.doi.org/10.1039/c39910001137.

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10

Bruce, Ian, Nigel G. Cooke, Louis J. Diorazio, Roger G. Hall, and Ed Irving. "ChemInform Abstract: Synthesis of the Carbocyclic Analogue (X) of (.+-.)-Rocaglamide (XII)." ChemInform 30, no. 32 (June 14, 2010): no. http://dx.doi.org/10.1002/chin.199932247.

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11

Malona, John A., Kevin Cariou, and Alison J. Frontier. "Nazarov Cyclization Initiated by Peracid Oxidation: The Total Synthesis of (±)-Rocaglamide." Journal of the American Chemical Society 131, no. 22 (June 10, 2009): 7560–61. http://dx.doi.org/10.1021/ja9029736.

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12

Trost, Barry M., Paul D. Greenspan, Bingwei V. Yang, and Mark G. Saulnier. "An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (-)-rocaglamide." Journal of the American Chemical Society 112, no. 24 (November 1990): 9022–24. http://dx.doi.org/10.1021/ja00180a081.

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13

Schoop, Andreas, Helmut Greiving, and Axel Goehrt. "ChemInform Abstract: A New Analogue of Rocaglamide by an Oxidative Dihydrofuran Synthesis." ChemInform 31, no. 25 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200025218.

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14

Dobler, Markus R., Ian Bruce, Fredrik Cederbaum, Nigel G. Cooke, Louis J. Diorazio, Roger G. Hall, and Ed Irving. "ChemInform Abstract: Total Synthesis of (.+-.)-Rocaglamide (Xa) and Some Aryl Analogues (Xb)." ChemInform 33, no. 7 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200207245.

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15

Wang, Xianyou, Dongjun Gong, and Zhaohai Qin. "Synthesis of Key Intermediate of Rocaglamide via SmI2 Catalyzed Intramolecular Reductive Coupling Reaction." Asian Journal of Chemistry 26, no. 23 (2014): 7973–76. http://dx.doi.org/10.14233/ajchem.2014.16838.

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16

Li, Hongsen, B. Fu, M. A. Wang, N. Li, W. J. Liu, Z. Q. Xie, Y. Q. Ma, and Zhaohai Qin. "Total Synthesis and Biological Activity of (±)-Rocaglamide and Its 2,3-Di-epi Analogue." European Journal of Organic Chemistry 2008, no. 10 (April 2008): 1753–58. http://dx.doi.org/10.1002/ejoc.200700905.

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17

Davey, Andrew E., and Richard J. K. Taylor. "A novel 1,3-dithiane-based cyclopenta-annellation procedure: synthesis of the rocaglamide skeleton." Journal of the Chemical Society, Chemical Communications, no. 1 (1987): 25. http://dx.doi.org/10.1039/c39870000025.

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18

Davey, Andrew E., Marcel J. Schaeffer, and Richard J. K. Taylor. "Synthesis of the novel anti-leukaemic tetrahydrocyclopenta[b]benzofuran, rocaglamide and related synthetic studies." Journal of the Chemical Society, Perkin Transactions 1, no. 20 (1992): 2657. http://dx.doi.org/10.1039/p19920002657.

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19

TROST, B. M., P. D. GREENSPAN, B. V. YANG, and M. G. SAULNIER. "ChemInform Abstract: An Unusual Oxidative Cyclization. A Synthesis and Absolute Stereochemical Assignment of (-)-Rocaglamide." ChemInform 22, no. 10 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199110308.

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20

Giese, Matthew W., and William H. Moser. "Stereoselective Synthesis of the Rocaglamide Skeleton via a Silyl Vinylketene Formation/[4 + 1] Annulation Sequence." Organic Letters 10, no. 19 (October 2, 2008): 4215–18. http://dx.doi.org/10.1021/ol801435j.

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21

Feldman, Ken S., and Christopher J. Burns. "Radical-mediated intramolecular [3-atom + 2-atom] addition and the synthesis of (.+-.)-rocaglamide: model studies." Journal of Organic Chemistry 56, no. 15 (July 1991): 4601–2. http://dx.doi.org/10.1021/jo00015a008.

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22

Rodrigo, Christina M., Regina Cencic, Stéphane P. Roche, Jerry Pelletier, and John A. Porco. "Synthesis of Rocaglamide Hydroxamates and Related Compounds as Eukaryotic Translation Inhibitors: Synthetic and Biological Studies." Journal of Medicinal Chemistry 55, no. 1 (December 19, 2011): 558–62. http://dx.doi.org/10.1021/jm201263k.

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23

Zhou, Zhe, and Marcus A. Tius. "Synthesis of Each Enantiomer of Rocaglamide by Means of a Palladium(0)-Catalyzed Nazarov-Type Cyclization." Angewandte Chemie 127, no. 20 (March 30, 2015): 6135–38. http://dx.doi.org/10.1002/ange.201501374.

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24

DAVEY, A. E., M. J. SCHAEFFER, and R. J. K. TAYLOR. "ChemInform Abstract: Synthesis of the Novel Anti-Leukaemic Tetrahydrocyclopenta(b) benzofuran, Rocaglamide and Related Synthetic Studies." ChemInform 24, no. 6 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199306310.

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25

Zhou, Zhe, and Marcus A. Tius. "Synthesis of Each Enantiomer of Rocaglamide by Means of a Palladium(0)-Catalyzed Nazarov-Type Cyclization." Angewandte Chemie International Edition 54, no. 20 (March 30, 2015): 6037–40. http://dx.doi.org/10.1002/anie.201501374.

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26

FELDMAN, K. S., and C. J. BURNS. "ChemInform Abstract: Radical-Mediated Intramolecular (3-Atom + 2-Atom)Addition and the Synthesis of (.+-.)-Rocaglamide: Model Studies." ChemInform 22, no. 52 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199152166.

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27

Zhou, Zhe, and Marcus A. Tius. "ChemInform Abstract: Synthesis of Each Enantiomer of Rocaglamide by Means of a Palladium(0)-Catalyzed Nazarov-Type Cyclization." ChemInform 46, no. 37 (August 27, 2015): no. http://dx.doi.org/10.1002/chin.201537228.

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28

Hailes, Helen C., Ralph A. Raphael, and James Staunton. "A biomimetic approach to the synthesis of rocaglamide based on a photochemical [2+2] cycloaddition of a cinnamate unit to a flavone." Tetrahedron Letters 34, no. 33 (August 1993): 5313–16. http://dx.doi.org/10.1016/s0040-4039(00)73983-9.

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29

Gerard, Baudouin, Sheharbano Sangji, Daniel J. O'Leary, and John A. Porco. "Enantioselective Photocycloaddition Mediated by Chiral Brønsted Acids: Asymmetric Synthesis of the Rocaglamides." Journal of the American Chemical Society 128, no. 24 (June 2006): 7754–55. http://dx.doi.org/10.1021/ja062621j.

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30

"Total Synthesis of (+)- and (–)-Rocaglamide." Synfacts 11, no. 06 (May 18, 2015): 0574–75. http://dx.doi.org/10.1055/s-0034-1380784.

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31

DAVEY, A. E., and R. J. K. TAYLOR. "ChemInform Abstract: A Novel 1,3-Dithiane-Based Cyclopenta-Anellation Procedure: Synthesis of the Rocaglamide Skeleton." ChemInform 18, no. 23 (June 9, 1987). http://dx.doi.org/10.1002/chin.198723327.

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32

Giese, Matthew W., and William H. Moser. "ChemInform Abstract: Stereoselective Synthesis of the Rocaglamide Skeleton (V) via a Silyl Vinylketene Formation/[4 + 1] Annulation Sequence." ChemInform 40, no. 6 (February 10, 2009). http://dx.doi.org/10.1002/chin.200906214.

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33

Wilde, Blake R., Mohan R. Kaadige, Katrin P. Guillen, Andrew Butterfield, Bryan E. Welm, and Donald E. Ayer. "Protein synthesis inhibitors stimulate MondoA transcriptional activity by driving an accumulation of glucose 6-phosphate." Cancer & Metabolism 8, no. 1 (December 2020). http://dx.doi.org/10.1186/s40170-020-00233-6.

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Abstract Background Protein synthesis is regulated by the availability of amino acids, the engagement of growth factor signaling pathways, and adenosine triphosphate (ATP) levels sufficient to support translation. Crosstalk between these inputs is extensive, yet other regulatory mechanisms remain to be characterized. For example, the translation initiation inhibitor rocaglamide A (RocA) induces thioredoxin-interacting protein (TXNIP). TXNIP is a negative regulator of glucose uptake; thus, its induction by RocA links translation to the availability of glucose. MondoA is the principal regulator of glucose-induced transcription, and its activity is triggered by the glycolytic intermediate, glucose 6-phosphate (G6P). MondoA responds to G6P generated by cytoplasmic glucose and mitochondrial ATP (mtATP), suggesting a critical role in the cellular response to these energy sources. TXNIP expression is entirely dependent on MondoA; therefore, we investigated how protein synthesis inhibitors impact its transcriptional activity. Methods We investigated how translation regulates MondoA activity using cell line models and loss-of-function approaches. We examined how protein synthesis inhibitors effect gene expression and metabolism using RNA-sequencing and metabolomics, respectively. The biological impact of RocA was evaluated using cell lines and patient-derived xenograft organoid (PDxO) models. Results We discovered that multiple protein synthesis inhibitors, including RocA, increase TXNIP expression in a manner that depends on MondoA, a functional electron transport chain and mtATP synthesis. Furthermore, RocA and cycloheximide increase mtATP and G6P levels, respectively, and TXNIP induction depends on interactions between the voltage-dependent anion channel (VDAC) and hexokinase (HK), which generates G6P. RocA treatment impacts the regulation of ~ 1200 genes, and ~ 250 of those genes are MondoA-dependent. RocA treatment is cytotoxic to triple negative breast cancer (TNBC) cell lines and shows preferential cytotoxicity against estrogen receptor negative (ER−) PDxO breast cancer models. Finally, RocA-driven cytotoxicity is partially dependent on MondoA or TXNIP. Conclusions Our data suggest that protein synthesis inhibitors rewire metabolism, resulting in an increase in mtATP and G6P, the latter driving MondoA-dependent transcriptional activity. Further, MondoA is a critical component of the cellular transcriptional response to RocA. Our functional assays suggest that RocA or similar translation inhibitors may show efficacy against ER− breast tumors and that the levels of MondoA and TXNIP should be considered when exploring these potential treatment options.

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34

Greger, Harald. "Comparative phytochemistry of flavaglines (= rocaglamides), a group of highly bioactive flavolignans from Aglaia species (Meliaceae)." Phytochemistry Reviews, June 4, 2021. http://dx.doi.org/10.1007/s11101-021-09761-5.

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AbstractFlavaglines are formed by cycloaddition of a flavonoid nucleus with a cinnamic acid moiety representing a typical chemical character of the genus Aglaia of the family Meliaceae. Based on biosynthetic considerations 148 derivatives are grouped together into three skeletal types representing 77 cyclopenta[b]benzofurans, 61 cyclopenta[bc]benzopyrans, and 10 benzo[b]oxepines. Apart from different hydroxy, methoxy, and methylenedioxy groups of the aromatic rings, important structural variation is created by different substitutions and stereochemistries of the central cyclopentane ring. Putrescine-derived bisamides constitute important building blocks occurring as cyclic 2-aminopyrrolidines or in an open-chained form, and are involved in the formation of pyrimidinone flavaglines. Regarding the central role of cinnamic acid in the formation of the basic skeleton, rocagloic acid represents a biosynthetic precursor from which aglafoline- and rocaglamide-type cyclopentabenzofurans can be derived, while those of the rocaglaol-type are the result of decarboxylation. Broad-based comparison revealed characteristic substitution trends which contribute as chemical markers to natural delimitation and grouping of taxonomically problematic Aglaia species. A wide variety of biological activities ranges from insecticidal, antifungal, antiprotozoal, and anti-inflammatory properties, especially to pronounced anticancer and antiviral activities. The high insecticidal activity of flavaglines is comparable with that of the well-known natural insecticide azadirachtin. Comparative feeding experiments informed about structure–activity relationships and exhibited different substitutions of the cyclopentane ring essential for insecticidal activity. Parallel studies on the antiproliferative activity of flavaglines in various tumor cell lines revealed similar structural prerequisites that let expect corresponding molecular mechanisms. An important structural modification with very high cytotoxic potency was found in the benzofuran silvestrol characterized by an unusual dioxanyloxy subunit. It possessed comparable cytotoxicity to that of the natural anticancer compounds paclitaxel (Taxol®) and camptothecin without effecting normal cells. The primary effect was the inhibition of protein synthesis by binding to the translation initiation factor eIF4A, an ATP-dependent DEAD-box RNA helicase. Flavaglines were also shown to bind to prohibitins (PHB) responsible for regulation of important signaling pathways, and to inhibit the transcriptional factor HSF1 deeply involved in metabolic programming, survival, and proliferation of cancer cells. Flavaglines were shown to be not only promising anticancer agents but gained now also high expectations as agents against emerging RNA viruses like SARS-CoV-2. Targeting the helicase eIF4A with flavaglines was recently described as pan-viral strategy for minimizing the impact of future RNA virus pandemics.

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